The synthesis of nucleosides (28a) and (28b) is described.* / The best procedure consisted of a five step synthesis from 5-methyluridine. Simultaneous protection of the 3'- and 5' -hydroxyl groups of 5-methyluridine with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl gave nucleoside (11). Base protection of nucleoside (11 ) with (trimethylsilyl)ethoxymethyl chloride provided product ( 24). It was transformed to its allyl ether (23) by reaction with allyl bromide and silver (11) oxide. Oxidation of ( 23) with N-methylmorpholine N-oxide and osmium tetroxide, followed by sodium metaperiodate afforded aldehyde (27). Desilylation of aldehyde (27) gave the desired nucleosides (28a) and (28b).* / 1H-NMR analysis of the diacetylated forms of the nucleosides indicated that both acetates at the newly formed anomeric center were in an axial conformation, and that structures and conformations (28a) and (28b) are a good representation for the two isomeric diols.* / Dimerization of nucleosides (28a) and (28b) are to be explored.* / *Please refer to dissertation for diagrams.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.20291 |
| Date | January 1997 |
| Creators | Tomasino, Tonino. |
| Contributors | Just, George (advisor) |
| Publisher | McGill University |
| Source Sets | Library and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada |
| Language | English |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Format | application/pdf |
| Coverage | Master of Science (Department of Chemistry.) |
| Rights | All items in eScholarship@McGill are protected by copyright with all rights reserved unless otherwise indicated. |
| Relation | alephsysno: 001609814, proquestno: MQ44300, Theses scanned by UMI/ProQuest. |
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